Sodium Carbonate → HCID 59272478, Verbindung

HRID 558154Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 558154
[N:1]1([CH2:6][CH2:7][NH:8][C:9]2[N:14]=[C:13]([C:15]3[S:19][C:18]4[C:20](B5OC(C)(C)C(C)(C)O5)=[CH:21][CH:22]=[CH:23][C:17]=4[CH:16]=3)[C:12]([F:33])=[CH:11][N:10]=2)[CH:5]=[CH:4][N:3]=[N:2]1.Br[C:35]1[CH:36]=[C:37]([F:44])[CH:38]=[C:39]2[C:43]=1[NH:42][CH:41]=[CH:40]2.O.O.O.O.O.O.O.O.[OH-].[Ba+2].[OH-].C(=O)([O-])[O-].[Na+].[Na+].C(=O)([O-])[O-].[K+].[K+].[F-].[Cs+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O.CS(C)=O.O1CCOCC1.CN(C=O)C>[N:1]1([CH2:6][CH2:7][NH:8][C:9]2[N:14]=[C:13]([C:15]3[S:19][C:18]4[C:20]([C:35]5[CH:36]=[C:37]([F:44])[CH:38]=[C:39]6[C:43]=5[NH:42][CH:41]=[CH:40]6)=[CH:21][CH:22]=[CH:23][C:17]=4[CH:16]=3)[C:12]([F:33])=[CH:11][N:10]=2)[CH:5]=[CH:4][N:3]=[N:2]1

Komponenten

12

Edukt 6

HCID 10340Sodium CarbonateHCID 11430Potassium CarbonateHCID 25953Cesium fluorideHCID 38528797-bromo-5-fluoro-1H-indoleHCID 17749109Barium hydroxide, octahydrateHCID 66738069HCID 66738069, Verbindung

Produkt 1

HCID 59272478HCID 59272478, VerbindungAusbeute 43,1 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Combine N-(2-(1H-1,2,3-triazol-1-yl)ethyl)-5-fluoro-4-(7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[b]thiophen-2-yl)pyrimidin-2-amine (0.12 g, 0.26 mmol), 7-bromo-5-fluoro-1H-indole (64 mg, 0.28 mmol, synthesized based on reference: Manfred S.; Assunta G.: Frédéric L., Eur. J. Org. Chem. 2006, 2956-2069), barium hydroxide octahydrate (0.24 g, 0.77 mmol, alternatively sodium carbonate, potassium carbonate, cesium fluoride), Pd(dppf)Cl2 (20 mg, 0.03 mmol) in 2 mL of mixed solvent of DMF (alternatively dioxane, DMSO) and water (4/1, v/v). Purge the mixture with N2 three times. Heat the reaction mixture to 80° C. for 4 h (HPLC monitor) (or microwave reactor). Cool to RT. Dilute with chloroform/IPA (3:1, v/v) 50 mL. Wash with water, aqueous saturated sodium chloride and dry over magnesium sulfate. Remove the organic solvent to give the crude product. Purify the residue by column chromatography (hexane to ethyl acetate, or methylene chloride and methanol) to give the title compound (0.053 g, 43%). MS (ES) m/z 474 [M+1]+.

Aufarbeitung

  1. customPurge the mixture with N2 three times
  2. temperatureCool to RT
  3. additionDilute with chloroform/IPA (3:1
  4. washWash with water, aqueous saturated sodium chloride
  5. dry with materialdry over magnesium sulfate
  6. customRemove the organic solvent
  7. customto give the crude product
  8. customPurify the residue by column chromatography (hexane to ethyl acetate, or methylene chloride and methanol)

Quellen und Nachweise

ORD-Eintrag
ord-e17a4f135a9e4fbcb4abdc1921746228
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063035B2

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